Warning: This story is a work of fiction and contains descriptions of explicit sexual acts between men and women. If this type of content offends you or you are under the age of 18 do not read it.
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Introduction to real cock as a sissy. MMM, MF, bi, anal, cd, toys *****
This all started when I'd become friends with the neighbor across the street. Jenny was both someone I hung out with because we had kids in the same grade at school and someone I noticed because she was well put together. Red hair, blue eyes, noticeable boobs, tight ass. Yeah, basically a milf.
Over time, our conversations became more personal as we got to know each other better and enjoyed the same types of humor and common experiences. It had been slowly progressing but there was definite chemistry between us and the time together became more intimate.
"What type of things turn you on"? she asked.
"Hmmm. You first."
"Well, I'm a bit of a tease at first but then I like to have it my way. I like to be in charge, I like toys, I like to have my pussy licked, and I like a little bondage and domination on occasion. Now you."
"I'm a little more passive in what turns me on. I like it when the woman takes charge."
"Takes charge how? What really turns you on?"
"I'm not sure this is a good topic." All I could think about was that the further we got into my sexual interests, the less interested she'd be in me.
"Oh, it's a great topic. I love talking about sex and I've been trying to get you to open up for the last 6 months. I really want to know what turns you on. What do you fantasize about?"
"Big gulp. Generally my fantasies are around domination and submission."
"So you're the bottom? Are you a bottom with your wife?"
"No. She doesn't really get into those types of scenes or fantasies. She just likes `normal' sex."
"Normal huh. Is that normal like boring?"
"Well she is a little more, ok a lot more, conservative. Different positions are fine. Oral sex is fine. But that is pretty much it."
"Do you like oral sex? Giving or getting? Any thing kinky?"
"Yes I do! Either, or and both. Even at the same time. I enjoy creampie but it's not something she likes doing."
"You like eating her after?"
"Yeah. Do you think that's gross?"
"No, I think it's hot, but most guys don't want to be eating and swallowing cum. Is that why you think you're more of the bottom?"
"That's really the only part to my fantasies that I've acted out with her. Most of the other stuff is just fantasies and playing with myself."
"You have to tell me about your fantasies. I told you mine."
"No you didn't all you said was you like to be in charge. Does that mean you're a `top'?"
"Well, I'm definitely in charge with my husband. He likes it when I tie him up. He likes spankings -- well I like spanking him -- and he likes it when I show him off."
"Well even as a bottom, I'm not into spankings and pain. Bondage might be interesting, but not pain just for pain. No thanks."
"So what kind of submission fantasies do you have?"
"I've never really shared this with anyone before, but I like the idea of dressing up and then being treated like a woman. I like the idea of being made to do things -- that's the female domination part -- and being made to serve."
"Like a sissy? Do you have any women's clothes or anything?"
"Yes like a sissy. I have a bra and panties and pair of stockings. And I have a couple of toys."
"What kind of toys?"
"A butt plug, a femdoe, and a good size dong."
"Oooo, yeah. Has your wife used the femdoe on you?"
"No. Like I said, she isn't in to that much. I've tried the femdoe before but like the dong better."
"You like the dong `better'. I'd like to see that. Do you model?"
"I haven't modeled. In fact you're the first person I've even told. I think wife knows but isn't interested."
"We'll maybe we can get you to model. It might be fun. What do you think about or fantasize about when you're dressed? Do you look at any websites or surf the net?"
"There are couple of story sites I really like. Normally I fantasize about being made to dress as a woman and then am asked / made to act like one. Or more like a little slut."
"What is your favorite story?"
"There have been lots of them, but the one that sticks out the most is this one about a poker game. The guy hasa bunch of friends over for a game and, in preparation, his wife makes him wear panties for the evening. About mid way through the game, she asks him `Are you ready to serve slut'?
"He realizes he has no choice and says yes.
"Then she proceeds to tell all of his friends that she made him wear her panties and that he will do anything she tells him to. She makes him show everyone the panties, and then sends him to get a big dildo from their toy chest. The show continues with him sucking the dildo in front of everyone until she comes. Then she asks who would like to be next?
"He basically sucks and fucks everyone at the table as they make him their slut.
"It's pretty hot all around, but the parts I like best are that she turns him into a total sissy slut for every one there and he loves it.
"Is that what you'd like? To be treated like a little sissy slut and made to serve?"
"I don't know. It's a long way from reading stories and jacking off to really doing it. But it is pretty exciting to think about. I've got a huge hard-on just telling you the story."
"Oh, you poor boy."
And with that she changed to subject and started talking about something else. It was such a rapid segue that I didn't realize what had happened until her husband walked in and said "Hi" along with a quick kiss on his way through the house.
It was a couple of weeks before I was able to drop by and see her again, but it didn't take long for her to pick up where we left off.
"I was thinking about your story and curious if you'd like to try something new? I'd like to be your mistress and maybe we could change some of your fantasies into reality."
"What do you have in mind?" I asked.
"Part of the excitement is the surprise. But a couple of ground rules: you have do exactly what I ask and you have to respond `Yes Mistress' when we are playing."
"How do I know when we're playing?"
She laughed and said "You'll know mostly by your attire, but there might be other clues as well."
I thought about her proposal and responded "Yes Mistress".
She smiled in a way I'd not seen before. There was a bit of mischievousness as well as a sense of command in her demeanor that was a bit different for how things had been before. She started with "We are going to have a good time!" and then told me what she wanted me to do the next time I came over.
Could I actually go through with what Jenny had told me she wanted? This was a big step from the secret confines of your own bedroom and fantasy land. In truth, I was committed from the time I said "Yes Mistress". I wanted to be Jenny's little slut and what she had suggested was almost like one my fantasies to a T.
The preparation for our next visit started with making a trip to the mall. First, I was to remove all of my body hair. She was very specific. All of it below my ears. Then I needed to add a few things to my bra, panties, and stockings. She wanted to replace my black with red lingerie. The bra needed to be a C-cup, and I needed a camisole, a garter belt, a pair of shoes.
Once I'd gotten rid of the hair, the question was how could I actually go out of the house in the specified attire: camisole and bra with a thin white t-shirt (not much mystery there), thong and garter with low cut pants (no mistaking the thong from behind), and stockings. I didn't have to wear the 3" heels in public but I would have to bring them with and wear them once inside.
I arrived at her house dressed as required. On the front porch -- thankfully there was an entry way -- I removed my jacket and knocked on the door.
"Hi Michelle. Or would you prefer Shelley?"
It took me a second ... "Shelley would be nice." Jenny looked unbelievable. She was wearing a bustier that highlighted her breasts and covered her erect elongated nipples under a transparent silk covering. Under her transparent panties you could see her red bush neatly trimmed into a cute little heart. She completed the ensemble with matching stockings. What a way to answer the door.
"Let's not forget to include Mistress when addressing me. You will be punished for that."
This snapped me back to reality. "Yes Mistress."
"Come inside. We have lots to do today to make sure you're the kind of sissy slut we want you to be. Take off your pants and t-shirt and change your shoes. And next time I tell you what to wear to my house that is ALL I want you to wear. You can leave your jacket at home." She waited impatiently as I removed the t-shirt, pants, and put the shoes on.
"First we are going to complete your look for today. Follow me."
"Yes Mistress" as we walked back toward her master bedroom. Aptly named. Once in the bedroom, she said "We need to finish making you up. I have a nice wig for you, something that will give a bit more shape up top, and we need to add a bit of make-up. Once she was done, my face was made up with foundation, powder, and pretty red lipstick. I had shoulder length hair, c-cup titties with some very cool glue-on breasts, and my finger nails and toenails were painted a pretty red. Wow. It was an amazing transformation. I'd come in looking mostly like a guy in women's underwear but now looked very, very feminine. Except for the hard cock sticking out of my panties.
Jenny took a look at her work and said "Almost there. Just two more things we need to take care of. Bend over the counter." As I leaned over I could feel the weight of my breasts pulling against my chest and I could see the nipples peaking back at me in the mirror. "Spread your legs" she said from behind me. In her hand was a tube of lube so I had a pretty good idea what she had in mind as she pushed my thong aside and pushed a well lubed finger, then two, inside of me.
"Now we come to the punishment part of today. Do you understand that I need you to do exactly what I say and that I expect to be treated with respect?"
"Yes Mistress" I responded.
"I'm sure you will slut but today got off to a rocky start. Originally I was going to introduce you to a medium plug," she said holding a plug that was about the size of mine in her hand. "But because you can't follow simple instructions, we'll start with something a little larger". In her hand was a very good sized plug with a nice dollop of lube spread over it.
Normally it will take a few minutes to fully stretch and fill myself. Both because I like the feeling and it can hurt if I take too much to soon. Jenny was a bit more insistent. "I hope you like being filled and stretched today" was all she offered as pushed it in with about four in / out strokes and I felt is pop inside and Jenny slide my panties back in place. There were tears in my eyes and I was biting my hand to recover from the ouch that came with it.
"Turn around," she said after a moment, "we need take care of that one last thing." She stepped closer and pushed me back against the counter and the pressure of the plug being pushed deeper felt very good. "We can't have a hot little slut walking around with a hard-on, so we'll need to get you some release." Her hand was on my cock and she began to jack me off. "Let's use your hand too." It wasn't long before I was ready to explode and she put a cup at the end of my penis. After about 5 long spurts into the cup I had finished and Jenny taped me back and out of the way to let the panties fit nicer.
"Tilt your head back, we don't want to mess up your make-up yet". As I did, the look in the mirror was amazing. My hair was draping over my shoulders, my tits were pushed up and out, and Jenny was pouring my cum in to my open mouth. "I hope you like the taste of cum" she said with a chuckle. There were about 3 good swallows from the cup and I enjoyed every drop.
She helped adjust my bra and camisole and handed me a pretty pink transparent "cover up" -- that covered nothing -- and led me back to the living room. To my surprise she had company. Her husband and a friend his were sitting there talking. "This must be your little sissy" her husband said.
"Actually Chuck, she is your little sissy for the rest of today" Jenny told her husband. "Shelley, you know my husband and this is our friend Tom. You are to do anything they ask. And I do mean anything."
"Yes Mistress" was all I could get out and Jenny just smiled.
"Shelley, could you get us another couple of beers?" was the first request. I responded with an appropriate "Yes Master" and went to find the kitchen. It took me a minute to find their beer stock -- it was in the back up fridge in the garage, which was wide open for all to see -- but I finally found it and brought them the two beers.
When I returned, they had settled into two recliners and looked to have gotten more comfortable. "That took you long enough. When we tell you to do something, we want it done quickly. Do you understand slut?"
"Yes Master. I'll do better."
"We'll see. From now on, when you're in the room with us, we want you on your knees. Crawl over here with our beer and hurry up." This "request" had come from Tom and I did exactly what he said. Once to the chairs, I popped open the beer and placed it on the table between them. "Who would you like to suck first?" Tom asked.
"You're company Tom so she can have you. Besides she will just love your cock. Go ahead and undo his pants Shelley, he has a nice surprise for you." I turned to Tom and moved in between his legs. There was an obvious bulge in his pants.
Tom undid the button and fly of his pants and put his hand on my shoulder and head to encourage me forward. As I opened his pants all the way, he wasn't wearing underwear and I was treated the sight of a very thick uncut cock. He was probably only 6" long but he was bigger around then the beer can I had just delivered.
"Go ahead. I like my balls licked too so get to it." With that I proceed to introduce myself to my first real cock. First licking him all over the balls and up the shaft and then trying to take him in my mouth. I could get the head in and a little bit of the shaft but he was so thick, there was no way to get it all. He shifted in the seat and got his pants all the way down as I stroked, licked, and sucked him. "I want my asshole licked, and not just a little flick. I want to feel your tongue in me" he said as he pulled his knees up to give me better access and pushed my head down. I started tentatively but with his moans and pressure on the back of my head I soon had my tongue pushed in deep.
With all of the activity I hadn't been thinking too much about Jenny. "Oooh. She has a lovely tongue. We'll have to get picture of that" and about that same time I saw that flash go off. With that Tom pulled me up and began to push his cock into my face. He was very tense and I put my mouth around him taking as much as I could. Another flash and Tom literally exploded into my mouth and face. I licked and swallowed as much as I could but there was no way to keep up. I had never seen so much cum before.
As Jenny ran the camera and the flash popped several more times I heard "Oh look at that little slut eat his cum". I had taken as much of it as I could and tried lick up the rest but that was still cum in my hair and all over my face.
"OK. My turn" Chuck said as I finished up with Tom. I had licked Tom enough that he was starting to get hard again. Looking over at Chuck, he was naked from the waste down and hard as rock. His cock was also about 6" long but a more normal thickness. I was actually looking forward to being able to take all of him in my mouth and enjoy him. Well it didn't take long for that to happen and I spent the next half hour with him fucking my mouth and enjoying having my nose in his pubic hair.
I know Jenny was busy taking pictures but I was enjoying just being a total slut and sucking her husband. Total was about to get a little bigger. I felt Jenny's hand on my ass and my panties being pushed aside. There was a tug on my butt blug and I was suddenly very empty and open. But not for long as I felt a pair have hands on my hips and a huge cock fill me up. Tom was back. Oh my god was he back. He was thicker than the plug had been and he was focused on giving me a very nice fucking.
My first time as a real slut and I have a cock in my mouth and another deep in my bottom. Once I adjusted they fell into a nice rhythm of fucking me. Tom came first. I think he just comes a lot because I felt totally flooded and when he pulled out I couldn't stop oozing cum. Just after I felt Tom spurting inside of me, I filled my panties with cum as well. We didn't cum at the same time but it was very close. Chuck held my head as he emptied his balls into my mouth. He didn't need to. I was going to devour and swallow every drop.
As I stood up, Jenny pulled me into her arms and gave me a long kiss. "You were wonderful. Let's go get cleaned up." We took a shower together and cleaned up the make-up and removed the breasts and wig to get back to normal. She made me wear my bra and panties home and I still had painted fingernails and toenails, but the rest is another story.
**** I hope you this was a big a thrill to read as it was to write. Feedback appreciated on both style and substance.